6,11-Dihydro-5H-dibenz[b,e]azepine → HCID 54506243, compound

HRID 355847Notes

Reaction equation

HRID 355847 reaction equation
[CH:1]1[C:11]2[CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH2:7][NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[N+:26]([O-:28])=[O:27])[C:20](Cl)=[O:21].C(N(C(C)C)CC)(C)C>ClCCl>[N+:26]([C:25]1[CH:24]=[CH:23][C:19]([C:20]([N:6]2[CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH2:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=3)=[O:21])=[CH:18][C:17]=1[CH3:16])([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 679746,11-Dihydro-5H-dibenz[b,e]azepineHCID 81531DiisopropylethylamineHCID 30157953-Methyl-4-nitrobenzoyl chloride

Product 1

HCID 54506243HCID 54506243, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.17 g of 6,11-dihydro-5H-di-benz[b,e]azepine, 1.20 g of 3-methyl-4-nitrobenzoyl chloride, 0.80 ml of diisopropylethylamine in 25 ml of dichloromethane is stirred 18 hours at room temperature. The mixture is washed with water and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate. The filtrate is concentrated and diluted while hot with hexane to give 1.40 g of crystals. Recrystallization from dichloromethane-hexane gives 1.26 g of crystals, m.p. 179°-180° C.

Workup

  1. washThe mixture is washed with water
  2. dry with materialdried (Na2SO4)
  3. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  4. concentrationThe filtrate is concentrated
  5. additiondiluted while hot with hexane

Sources & evidence

ORD record
ord-d6bbf1e08ea44f2aaa293eccbb51a41d
Source dataset
uspto-grants-1998_11
Patent number
US05834461

Reaction notes

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